Andrea Guest: 15 Years, a 6-Person Portland Team, and Her Push to Recruit Through AI

Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/ Guest Bio: Andrea Guest leads a six-person real estate team in Portland, Oregon, after a prior career in radio advertising sales in Las Vegas. Over 15 years she built her business from a solo agent into a team with dedicated operations and marketing support, and she remains heavily involved in personal production while actively recruiting more agents. Episode Summary: Andrea Guest walks through her transition from radio sales into real estate, the hiring lesson that changed her trajectory, and how her team structures lead generation, follow-up, and goal-setting today. She also shares where she's applying AI across her business and what she'd tell an agent trying to double their transactions. What's Covered: Andrea explains how she left a radio advertising sales career in Las Vegas and stumbled into real estate while planning to open a cafe, only to discover it fit her marketing and business interests far better. She describes her first hire as a mistake, a buyer's agent she wasn't ready for, and how bringing on an administrative professional to build systems was the real turning point that let her sell more. Andrea details a morning lead generation routine built around a CRM-driven priority list, covering hot clients, new leads, and longer-term nurtures, plus the paid lead channels and pay at closing programs her team uses. She lays out a tiered follow-up philosophy, from calling online leads within minutes to reaching out to hot clients daily and nurture leads quarterly, and explains why she never waits a full year even when a client says they are. Andrea shares how she coaches team members to lead generate through their own personal strengths and networks, from community charity work to a neighborhood pool league, while still pushing everyone toward call volume. She outlines how she's using AI for back-end efficiency, including CRM-integrated texting with cold leads, inspection report summaries, and blog and social content, and names recruiting more agents as the single change that would most impact her business. Timestamps: 00:00 - Introduction to Andrea Guest 00:34 - From radio sales to real estate 02:47 - Early struggles and the first hire mistake 04:01 - Growth mindset around losing team agents 05:50 - Current six-person team structure 08:06 - Morning lead generation routine 09:12 - Lead channels and pay at closing options 10:15 - How agents choose their own lead gen style 13:17 - Follow-up philosophy for new leads 21:50 - Follow-up timelines and staying in touch for years 21:43 - Rebuilding a business in a brand new market 20:05 - What's working right now: leaning into AI 24:37 - The one change that would have the biggest impact: recruiting 25:18 - Advice for doubling transactions from 12 a year